Bromisovaleric ester of the borneols.



Uid lTED STATfig MAX DOHRN, OF BERLIN, GERMANY, ASSIGNOR TO GHEMISGHE FABRIK AUF ACTIEN WORM.

i E. SCHER'ING), OF BERLIN, GERMANY.

BROMISOVALERIC ESTER OF THE BSBNEOLS.

Specification of Letters Patent.

' Patented Aug. 3, 1909.

Application filed February 19, 1908. Serial No. 416,686. (specimens) T all whom it may concern:

Be it knownthat I, MAX DOHRN, doctor of philosophy, chemist, citizen of the German Empire, residing at Berlin, Germany, have invented a new and useful Improvement in Bromisovaleric Acid Esters of the Borneols, of which the following is a'specification.

My invention relates to the manufacture of the hitherto unknown bromisovaleric acid esters of the borneolsborneol and isobornook-having the formula on on Br 000 c H H3/ l0 17 in which C H signifies the bornyl or isobornyl radical. They are colorless oily fluids, insoluble in water, soluble in organic solvents, for instance, alcohol, ether, benzol, chloroform and acetone, and possess me- 20 dicinally sedative properties. These esters may be prepared by allowing bromisovaleric acid-halogenid or anhydrid to react upon the borneols, or by treating bromisovaleric acid with the borneols in the presence of asuitable 2'5 condensing agent, or by brominating the borneol esters of isovaleric acid. The bromisovaleric acid isoborneol ester may also be obtained by allowing bromisovaleric acid to react upon camphene in the presence of a suitable condensing agent, such as giinc chlorid, sulfuric acid, hydrochloric acid, and the like.

' Examples.

mid or the equivalent quantity of the chlorid are heated on a water bath with 560 grams of borneol dissolved in about 1,800 grams of chloroform, until hydrobromic or hydrochloric acid is no longer evolved. The product of the reaction is washed with neutral dilute soda solution, separated from the water and dried by means of sodium sulfate. After distillation of the chloroform the bromisovaleric acid borneol ester is distilled in vacuo. It boils at 163 Centigrade under a pressure of 10 millimeters and is a colorless thick oily fluid. This reaction is illustrated by the following equation:

oncnnl-oooo s mmit .2. 500 grams of bromisovaleric acid anononmcooc, n +rno.

a 250 grams bromisovaleric acid are heated to about 7 0 to 86 cent-igrade with 200 grams of borneol with the addition (ii 20 grains of concentrated sulfuric acid. After about 20 hours Water 18 added to the product of the reaction which is then further treated as in the foregoing examples. This reaction 18 illustrated by the following equation:

/.GH.CHB\'.CO0H+C1OH17.OH= a H OH.UHBRCOOCWHH+1120,

4. 250 grams of hromin are added in drops 1301500 grams of isovaleric acid bornecl ester while heated on the water bath until the solution is colorless. In order to retain the *m r a ll iun r n te ma 1. 900 grams of bromlsovaleric acid brol hyd b 0mm i sod 1 b0 be added. The solution is afterward distilled "m cacao. This reaction is illustrated by the following equation:

cH.eriBi-.coo.o, u men.

chlorid by washing with Water, the bromisovaleric isoborne'dl ester produced is treated first with soda solution and then with water;

the product separated from the water is then I claim as my invention:- {is new chemical products the bromisova: leric esters of the borneols, obtainable in the herein described manner, answering the formula in which C H Lsignifies the bornyl or' iso- -bornyl radical, being colorless oily fluids,

insoluble. in water, soluble in organic solvents, and possessing sedative properties, 9

substantially as described.

In testimony whereof I have hereunto set my hand in the presence of two subscribing witnesses. o

- MAX DQHRN.

Witnesses:

- HENRY HAsPER,

WOLDEMAR HAUPT. 

